Tour of Foodie

Tour of Foodie

“We control the weather!” proclaims Colin Caplan, founder and president of Taste of New Haven food and drink tours. Two dozen eager tour participants cluster in Temple Plaza at high noon on a perfect September Sunday, sunny and mild, blue skies as far as the eye can see, and Caplan is so charismatic the crowd almost believes him.

He launched Taste of New Haven one year ago, and since then has led more than 1,200 people on 75 walking tours. Originally born and raised in New Haven, Caplan left the area to study architecture at Tulane, then lived in Los Angeles where he dabbled in a number of professions including actor, courier and caterer. Eventually he landed on culinary tour guide, working for a company called Six Taste.

Inspired by that gig in L.A., Caplan leveraged the experience to pursue a similar business model when he returned to New Haven. His extensive local knowledge doesn’t hurt; he’s written four published books on the history of New Haven and has more in the works.

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Caplan’s tours combine the elements of his background—love of history and architecture; quick wit and flair for the dramatic; love of food and food service—which add up to an afternoon that feels like an adult field trip with a nutty professor, packed with fun and fascinating information.

Today I’m taking one of ToNH’s Theater District tours. Caplan builds camaraderie from the get-go, asking everyone to share their name, town and favorite food. Then it’s off to a wine tasting at the Wine Thief.

“Morning is the best time to try wine,” says our host T.J., “because there’s no food polluting the taste buds yet.” We try two wines, a Spanish Albarino and an Austrian Pinot Noir, both under $20 a bottle, then Caplan directs us to the beer cases for a quick overview of local brews.

Next stop is Temple Grill for a half-portion of one of their best sellers, the grilled Ahi tuna sandwich with wasabi aioli and sides of waffle and sweet potato fries. While we wait for the food, stiff drinks are served, gin and tonics with a grapefruit and Elderflower liqueur twist. Caplan chats up co-owner Chris Candido and they both jump in to the narrative, taking turns in telling the story of Chris’s “triple great” grandfather, George Basserman, owner of Rock Brewery on State and Rock streets and a true visionary for selling beer on Sundays. Food arrives and conversation flows as participants get to know each other. Then Caplan gives a five-minute warning.

We head to BAR for pizza and architecture lessons. The restaurant space was created by merging two old maintenance garages dating from 1915. The group shares four huge pies and pitchers of house-brewed beer as Caplan delves into pizza history, reveals the origin of the term apizza, profiles Wooster Street key players, and highlights what makes New Haven pizza unique (for example, the coal-fired brick ovens, or the high-protein dough which makes for a dense, chewy crust).

Another two-minute warning and then we step across the street to pause at Louis’ Lunch. A head peeps from the doorway, listens to Caplan for a moment, then invites the entire group inside, a surprise even to Caplan. We hear about the late Ken Lassan, father and founder of Louis’ Lunch, and his passion for hamburgers and bricks. I’m impressed to find out there’s a brick collection built into the wall with bits of the Parthenon, the Alhambra, the Roman Coliseum, and the Taj Mahal.

We carry on with a walk along High Street. Caplan gathers the group at the steps of a Yale fraternity and points out five different architectural styles along the street: Gothic, Tudor, Romanesque, Italianate, and Greek Revival, describing the characteristics of each.

After ducking into the Yale Center for British Art lobby for a two-minute ode to the work of Louis Kahn, Caplan dashes across the street to Chocopologie, returning moments later with a box of signature chocolates for us to sample on the museum sidewalk. (The method to this madness is that the long, narrow store wouldn’t comfortably accommodate our whole group.)

The outdoor portion of the tour continues with our walk along High Street, stopping outside Skull and Bones Secret Society to hear the legend of Prescott Bush and the bones of Geronimo, as we make our way to the Elm Street Kettle Corn cart. We get a demo and a recipe, then free, hot samples of the sweet, salty, crunchy snack.

On the way to our last spot, we visit Yale’s Old Campus and the Nathan Hale statue; the New Haven Green to consider that it was once a graveyard; and the exterior of the Taft for a rundown of the theaters once thriving in the area. Afterward we relax at Kelly’s, where co-owner Patrick provides background on how he and his wife Linda came to New Haven via Ireland on the way to Australia (spoiler alert: they never made it). Patrick offers the group a choice of beers and we each get a sampler plate of crab cake croquettes, peanut encrusted brie and pulled pork quesadillas.

It’s nearly dinnertime, and no one is in any rush to leave. After five hours of appreciating, learning and eating, our hearts, minds and stomachs are full. Then Caplan, who had quietly slipped out during Patrick’s, returns with one more dessert—mango and black sesame mochi ice cream from The Mochi Store nearby—and, as we’ve done all day, we manage to find a little more room.

Taste of New Haven
203-710-3710 |

Written and photographed by Jane Rushmore.

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Jane Rushmore specializes in travel stories and food reviews. She’s published articles on topics across the globe, such as palaces in Thailand, mineral spas in the Czech Republic, and opera festivals in Northern Italy. After brief periods living in London and Australia, she is happy to call New Haven home for the past decade.

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